This trophy/achievement is related to the optional story mission 'Special Delivery'. This mission is the final mission in Nick Rye's questline.

Simply, head to Rye & Son's Airfield in John's region, progress through his missions until reaching Special Delivery. To see the exact details of this trophy, see the guide below.

SPOILER WARNING: There are spoilers below.

This mission is simple, all your character needs to do is drive from Nick's house to the Midwife's home. There are a lot of obstacles to dodge, but other than that this mission is simple to complete. Upon finishing the mission the trophy/achievement will unlock.